Head of Sales

Head of Sales

Location: Tyler, TX (Remote/hybrid possible for candidates in the DFW area)

Reports to: CEO

Employment Type: Full-Time, W2, Direct Hire

Base Pay Range: $/yr – $/yr

Compensation Includes: variable compensation accelerators, commission and revenue share paid quarterly.

Travel: Regional trade shows and internal meetings in Tyler, TX. Company cannot sponsor a Visa.

Company: Privately held payments and technology company with over 20 years of operating history and approximately 80 full time employees and contractors. It operates as a registered ISO and serves merchants nationwide through direct sales, ISO partners, and reseller relationships. The company’s product lines include payment processing, a POS, and a newly acquired and evolving gateway platform. Approximately 60 % of revenue comes from restaurants and hospitality, with the remainder from retail.

The POS product recently completed a full transition to a cloud‑based platform in July 2025, following earlier reputational challenges tied to a legacy peer‑to‑peer tablet architecture. The firm is now focused on rebuilding trust, restoring sales momentum, and driving growth across all product lines.

This hands‑on sales leadership role is responsible for reversing a recent sales decline, rebuilding customer and partner trust, and driving sustained revenue growth across the company’s product lines, with an immediate focus on the POS product and gateway solutions. The Head of Sales will lead sales recovery efforts, reengage lost customers and partners, manage and develop the existing sales team, and align sales execution with marketing, product, onboarding, and support.

This role requires active selling—calling former customers, running demos, closing deals, coaching reps live—and quick execution in an imperfect, fast‑moving environment.

• Lead sales recovery and growth efforts across POS, payments, and gateway products.
• Personally engage and win back churned customers, resellers, and partners.
• Rebuild trust and market credibility following the POS platform rewrite.
• Restore sales performance to prior‑year levels within six months and exceed them within twelve months.
• Manage and coach an onsite team of three to four sales reps through daily, weekly, and monthly cadences.
• Establish and enforce clear standards for qualification, demos, follow‑up, and closing.
• Build a predictable and scalable sales pipeline and forecasting process.
• Own key performance metrics: new unit sales, win‑back conversion, close rate, sales cycle length, and retention impact.
• Partner closely with marketing on lead quality, messaging, and campaigns.
• Work with product, onboarding, and support teams to ensure smooth implementation and customer success.
• Support reseller and ISO partner onboarding, enablement, and growth.
• Manage and scale Salesforce, including reporting, pipeline visibility, and KPI tracking.
• Represent the company at regional trade shows and industry events.

• 8+ years of sales experience with at least 5 years in a senior sales leadership role.
• Strong background in payments, POS, and fintech.
• Experience selling to restaurants, bars, small retail, and multi‑location merchants.
• Proven success onboarding and managing ISO or reseller partners, handling approximately 20 deals per month.
• Demonstrated experience leading sales turnarounds following product issues, churn, or reputational challenges.
• Comfortable with hands‑on selling, including calling prospects, running demos, and closing deals.
• Experience managing and growing a sales team.
• Knowledge of hardware, software, and onboarding‑based sales models.
• Strong objection‑handling skills related to past product issues, competitive comparisons, and support concerns.
• Ability to translate technical improvements into clear ROI‑driven customer value.
• Accountable, resilient, and comfortable operating without large budgets or perfect systems.
• High‑integrity leadership style focused on transparency, trust rebuilding, and execution. Operates in a flat, low‑bureaucracy environment where leaders are expected to execute, not delegate problems.

• Experience recruiting or supporting agent networks.
• Direct experience running win‑back or reactivation campaigns.
• Background working in flat, founder‑led organizations.

Seniority Level: Director

Job Function: Sales, Business Development, and Marketing

Industries: Financial Services, Banking, and Software Development